US3748324A - Method for the purification of sucrose esters of fatty acids - Google Patents
Method for the purification of sucrose esters of fatty acids Download PDFInfo
- Publication number
- US3748324A US3748324A US00009040A US3748324DA US3748324A US 3748324 A US3748324 A US 3748324A US 00009040 A US00009040 A US 00009040A US 3748324D A US3748324D A US 3748324DA US 3748324 A US3748324 A US 3748324A
- Authority
- US
- United States
- Prior art keywords
- sucrose
- sucrose ester
- water
- acid
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract description 88
- 239000001959 sucrose esters of fatty acids Substances 0.000 title abstract description 36
- 235000010965 sucrose esters of fatty acids Nutrition 0.000 title abstract description 36
- 238000000746 purification Methods 0.000 title abstract description 23
- 229930006000 Sucrose Natural products 0.000 abstract description 194
- 239000005720 sucrose Substances 0.000 abstract description 194
- -1 SUCROSE ESTER Chemical class 0.000 abstract description 163
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 134
- 239000000203 mixture Substances 0.000 abstract description 89
- 238000011282 treatment Methods 0.000 abstract description 88
- 239000003960 organic solvent Substances 0.000 abstract description 74
- 150000003839 salts Chemical class 0.000 abstract description 70
- 239000011541 reaction mixture Substances 0.000 abstract description 63
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical class O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 abstract description 48
- 239000002253 acid Substances 0.000 abstract description 40
- 238000000354 decomposition reaction Methods 0.000 abstract description 31
- 239000000126 substance Substances 0.000 abstract description 27
- 238000000622 liquid--liquid extraction Methods 0.000 abstract description 26
- 238000000638 solvent extraction Methods 0.000 abstract description 26
- 238000001556 precipitation Methods 0.000 abstract description 25
- 239000012535 impurity Substances 0.000 abstract description 15
- 229960004793 sucrose Drugs 0.000 description 191
- 239000010410 layer Substances 0.000 description 83
- 235000002639 sodium chloride Nutrition 0.000 description 82
- 235000014113 dietary fatty acids Nutrition 0.000 description 75
- 239000000194 fatty acid Substances 0.000 description 75
- 229930195729 fatty acid Natural products 0.000 description 75
- 150000004665 fatty acids Chemical class 0.000 description 75
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000007787 solid Substances 0.000 description 47
- 239000002904 solvent Substances 0.000 description 45
- 239000012044 organic layer Substances 0.000 description 44
- 239000002244 precipitate Substances 0.000 description 43
- 239000003945 anionic surfactant Substances 0.000 description 38
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000004094 surface-active agent Substances 0.000 description 29
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
- 238000001953 recrystallisation Methods 0.000 description 23
- 239000007795 chemical reaction product Substances 0.000 description 19
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 18
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 17
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 17
- 238000004945 emulsification Methods 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 235000021355 Stearic acid Nutrition 0.000 description 15
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 15
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 15
- 239000008117 stearic acid Substances 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 14
- 235000015278 beef Nutrition 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 239000011780 sodium chloride Substances 0.000 description 14
- 150000003445 sucroses Chemical class 0.000 description 14
- 239000003760 tallow Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- 239000002195 soluble material Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 239000000344 soap Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 229910019142 PO4 Inorganic materials 0.000 description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 11
- 235000021317 phosphate Nutrition 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 10
- 125000000129 anionic group Chemical group 0.000 description 10
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 238000002203 pretreatment Methods 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 10
- 229910001629 magnesium chloride Inorganic materials 0.000 description 9
- 235000011147 magnesium chloride Nutrition 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 7
- 150000003863 ammonium salts Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000011259 mixed solution Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 230000001105 regulatory effect Effects 0.000 description 7
- 238000000956 solid--liquid extraction Methods 0.000 description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000001110 calcium chloride Substances 0.000 description 6
- 229910001628 calcium chloride Inorganic materials 0.000 description 6
- 235000011148 calcium chloride Nutrition 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000010446 mirabilite Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 235000007686 potassium Nutrition 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 229960003975 potassium Drugs 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000004996 alkyl benzenes Chemical class 0.000 description 5
- 150000008051 alkyl sulfates Chemical class 0.000 description 5
- 150000008052 alkyl sulfonates Chemical class 0.000 description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 5
- HLKMEIITONDPGG-UHFFFAOYSA-L barium(2+);2-hydroxypropanoate Chemical compound [Ba+2].CC(O)C([O-])=O.CC(O)C([O-])=O HLKMEIITONDPGG-UHFFFAOYSA-L 0.000 description 5
- 230000033228 biological regulation Effects 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000004310 lactic acid Substances 0.000 description 5
- 235000014655 lactic acid Nutrition 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000001630 malic acid Substances 0.000 description 5
- 235000011090 malic acid Nutrition 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 230000020477 pH reduction Effects 0.000 description 5
- 239000001103 potassium chloride Substances 0.000 description 5
- 235000011164 potassium chloride Nutrition 0.000 description 5
- 159000000001 potassium salts Chemical class 0.000 description 5
- 239000001384 succinic acid Substances 0.000 description 5
- 235000011044 succinic acid Nutrition 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 4
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 235000011837 pasties Nutrition 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 239000004323 potassium nitrate Substances 0.000 description 4
- 235000010333 potassium nitrate Nutrition 0.000 description 4
- 229940090181 propyl acetate Drugs 0.000 description 4
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- 235000017281 sodium acetate Nutrition 0.000 description 4
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 4
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000001540 sodium lactate Substances 0.000 description 4
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- 229940005581 sodium lactate Drugs 0.000 description 4
- 239000001488 sodium phosphate Substances 0.000 description 4
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- 235000019830 sodium polyphosphate Nutrition 0.000 description 4
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
- 235000019345 sodium thiosulphate Nutrition 0.000 description 4
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
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- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
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- 239000003054 catalyst Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
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- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
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- 239000000843 powder Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 150000005691 triesters Chemical class 0.000 description 3
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 2
- CCCIYAQYQZQDIZ-UHFFFAOYSA-N 6-methylheptan-3-one Chemical compound CCC(=O)CCC(C)C CCCIYAQYQZQDIZ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940072049 amyl acetate Drugs 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 2
- 229940117955 isoamyl acetate Drugs 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229940017219 methyl propionate Drugs 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 229940096992 potassium oleate Drugs 0.000 description 2
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 229960001763 zinc sulfate Drugs 0.000 description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- VPSXHKGJZJCWLV-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(1-ethylpiperidin-4-yl)oxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OC1CCN(CC1)CC VPSXHKGJZJCWLV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229960002737 fructose Drugs 0.000 description 1
- 229960001031 glucose Drugs 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229960001516 silver nitrate Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 229940013123 stannous chloride Drugs 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
Definitions
- This invention relates to a process for the purification of sucrose (or saccharose) esters of fatty acids, more particularly, to a process for the purification of sucrose esters of fatty acids (hereinafter referred to as SE) from crude reaction mixtures or the like compositions containing such sucrose esters.
- sucrose or saccharose
- crude reaction products made by such processes include in their solid body about 10 to 80% of SE, about 2 to 50% of non-reacted sucrose, about 3,748,324. Patented July 24, 1973 5 to 40% of anionic surface active agent, 1% or less of coloring and odor substances and other reaction residues.
- the most important problem to be solved is to remove various impurities contained in the crude reaction products in an economically as well as industrially acceptable manner.
- the invention is directed to the purification of the crude SE reaction products and the like compositions obtained by various conventional methods.
- the like compositions described hereinabove indicate various SE containing compositions and solutions for industrial use.
- SE containing crude reaction mixtures made by the so-called transparent emulsion method include in particular about 10 to 40% of anionic surface active agents hereinafter referred to as anionic surfactants. Since this portion of the anionic surfactant causes emulsification, none of the conventional processes for the purification of sucrose esters of fatty acids could be applicable to purify the crude reaction mixtures containing such anionic surfactant prepared by the transparent emulsifying method. Accordingly, a new effective purification process for such SE containing crude reaction mixture made by the transparent emulsion method has been desired. As disclosed in Japanese patent publication No.
- the crude reaction mixtures containing SE made by processes other than the transparent emulsion method generally comprise basic alkyl ester of fatty acid, sucrose ester of fatty acid formed by transesterification of natural or synthetic glycerides with sucrose, non-reacted sucrose, a small amount of soap-by-produced owing to the presence of catalyst,
- British patent specification No. 826,801 discloses a process for recovery of esters of sucrose from crude reaction mixtures containing such esters by using water and ketone solvent or ester solvent, this process can not be successfully applied to recover sucrose esters from the crude reaction mixtures prepared by the transparent emulsion method.
- the crude SE containing reaction mixtures made through the utilization of the transparent emulsion technique include among others a relatively large amount of anionic surfactant and this portion of the surfactant causes an undesirable emulsification which makes it difiicult to separate the organic and water phases from each other if the recovery of sucrose esters from the crude mixtures is carried out by such process as disclosed in the above British patent.
- sucrose ester is transferred in large amounts into the water phase, thus lowering the extraction efliciency. Moreover, any recrystallization, if subsequently carried out, cannot successfully separate the sucrose ester from the anionic surfactant.
- sucrose esters recovered by such processes include relatively large proportions of soap and unesterified sucrose which may result in poor purity thereof.
- the anionic surfactant exists not only in the crude reaction product for SE produced by the transparent emulsion method but also in any other like compositions containing SE which are produced by other methods or as a by-product of any other chemical process.
- Such anionic surfactants may be those added for carrying out the reaction or produced during such reaction. It is extremely difficult to separate such anionic surfactant from the crude reaction products or the like compositions containing the sucrose ester since the anionic surfactants and fatty acids exhibit substantially similar properties, in particular, solubility, to those of sucrose esters of fatty acid with respect to various solvents. Accordingly, a more efiicient process for the separation of anionic surfactants has long been desired, especially in the food industry where sucrose esters of fatty acids having a possible minimum content of surfactants are needed.
- the primary object of this invention is to provide a new and improved method for the purification of sucrose esters of fatty acids in which anionic surfactants can be particularly effectively removed from the crude reaction products or the like compositions containing such sucrose esters on an economically as well as industrially acceptable basis with a high yield of sucrose ester.
- the SE content in the crude reaction products described above comprises monoester, di-ester and other esters higher than diester.
- esters higher than monoester will be referred to as polyester.
- the monoester is highly appreciated as a epoch-making surfactant and already there is a great demand for the monoester because of its superior hydrophilic characteristics as compared with conventional innoxious surface active agents such as, for example, fatty acid esters of glycerin, sorbitau and propylene glycol.
- conventional innoxious surface active agents such as, for example, fatty acid esters of glycerin, sorbitau and propylene glycol.
- Another object of the invention is to provide a new and improved method for effectively isolating the monoester from polyesters contained in the crude reaction products described.
- a further object of the invention is to provide a new and useful method for the purification of sucrose esters of fatty acids in which different treatments for removing various impurities are combined successively according to the purposes for which the products are used.
- the process for the purification of sucrose esters of fatty acids from crude reaction mixtures or the like compositions containing such sucrose esters comprises the steps of: dissolving the crude reaction mixture or the like in a solution of a mixture of an organic solvent with water to form a system and removing impurities contained in said crude reaction mixture or the like dissolved in said solution whereby the sucrose ester is recovered.
- the step of removing impurities comprises subjecting said crude reaction mixture or the like to any one of the fol lowing treatments or their combinations:
- the above mentioned treatment (a) has been found particularly advantageous for the recovery of sucrose esters of fatty acids from SE containing crude reaction mixtures prepared by using the transparent emulsion technique and including a relatively large amount of anionic surfactant.
- a preferred embodiment of the invention is carried out by adding 1 part of the crude reaction mixture containing the sucrose ester of fatty acid, unesterified sucrose, anionic surfactant and a small amount of catalyst to the mixed solution comprising 3 to 10 parts of an organic solvent and 2 to 8 parts of water, adjusting the pH of said mixed solution at a value within the range of 3.5 to 5.0 with the addition of an acid sufficient to acidify the anionic surfactant and stirring the mixed solution at elevated temperatures until the constituents thereof are completely dissolved.
- the amount of water set forth above includes the amount of water when acid is to be added in to the form of an aqueous solution.
- the prepared system is allowed to separate into two distinct layers of water and organic solvent layers without causing emulsification. it would be more desirable to wash the separated water layer with 1 to 3 parts of a fresh amount of organic solvent and then to add the upper organic layer thereof to the initially separated organic solvent layer.
- the proportion of water to organic solvent in the mixed solution and the amount of the mixed solution to be used are suitably selected depending on the content of each of sucrose ester of fatty acid, unesterified sucrose and anionic surfactant in the crude reaction mixture described and/ or the number of carbon atoms of the fatty acid in the raw material for producing the crude reaction mixture de scribed.
- an insufiicient use of water may thwart ready liquid-liquid separation
- sucrose ester of fatty acid and acidified surfactant are extracted into the separate upper layer of organic solvent, while substantially all of the unesterified sucrose and salt are extracted into the lower water layer.
- a high yield of sucrose ester of fatty acid can be recovered by subjecting the upper organic solvent layer to a suitable drying treatment. In some applications it is possible, however, to use this layer of organic solvent without drying.
- the process according to this aspect of the invention may be followed, if necessary, by concentration and filtration at lower temperatures of the remaining organic layer to recover more purified sucrose ester of fatty acid.
- acids which are employed to acidify the surface active agent prior to the liquid-liquid extraction are chiefly acids which may include mineral acids such as hydrochloric acid, sulfuric acid, phosphoric acid and organic acids such as formic acid, acetic acid, lactic acid, malic acid and succinic acid. Acid salts such as acid sulfate and acid phosphate may also be used for this purpose.
- Suitable solvents which may be used for the liquidliquid extraction are methyl acetate, ethyl acetate, nhexane, toluene, benzene, xylene, methyl ethyl ketone, methyl isobutyl ketone and the mixtures thereof.
- the mixture of water and one or more of these organic solvents provides a preferred system in which the water and solvent are isolated from each other into two distinct layers without producing an emulsion. This facilitates an efiicient extraction of the sucrose ester of fatty acid.
- suitable pre-treatments may be given to the crude reaction mixtures described before the present process is carried out.
- One such pre-treatment involves the removal of considerable amounts of anionic surfactant and unesterified sucrose from the crude reaction mixture by putting the crude reaction mixture into an organic solvent to cause a solid-liquid extraction of the system.
- the extract obtained as the result of this pre-treatment could be used in the present process with or without removing the organic solvent therefrom.
- the other of such pre-treatments involves the removal of a substantial amount of unesterified sucrose from the crude reaction mixture by carrying out a liquid-liquid extraction with the addition to the crude reaction mixture of water and an organic solvent the same as the one which will be used for the liquid-liquid extraction in the present process.
- a substantial amount of unesterified sucrose is extracted out of the crude mixture into the aqueous phase.
- the same organic solvent as for the liquid-liquid extraction in the present process is preferably employed.
- the anionic surfactant contained in the crude reaction products or the like compositions can be removed by the before-mentioned treatment (b) as Well as by the treatment (a).
- the treatment (b) comprises adding to the system comprising a solution of the mixture of an organic solvent with water and crude reaction mixture or the like dissolved therein, a salt of a metal Whose valence is at least two to form double decomposition salts and then removing the double decomposition salts to recover the sucrose ester.
- the anionic surfactant contained in the crude reaction products described or the like could substantially be separated and removed therefrom by double-decomposing the surfactant into double-decomposition salts such as metallic soaps by addition of a salt of a metal whose valence is at least two. This naturally results in a substantial increase of SE yields.
- the treatment (b) is particularly advantageous for the purification of the crude reaction products produced by the so-called transparent emulsion method, the products of which generally contain a greater amount of anionic surfactant.
- Suitable metallic salts which may be used for the purpose of the treatment (b) are, for example, neutral, acidic and alkaline salts or complex salts or double salts of divalent or higher metals such as aluminum, barium, cobalt, lead, magnesium, manganese, copper, zinc, calcium, tin, silver and iron, or the mixtures of those salts.
- those salts there may be mentioned for example, aluminum hydroxide, barium hydroxide, calcium hydroxide, calcium chloride, magnesium chloride, magnesium sulfate, cupric chloride, cobalt chloride, zinc hydroxide, stannous chloride, calcium acetate, silver nitrate, bleaching powder and alums.
- These metallic salts may be used in an amount stoichiometrically equivalent to the amount of the anionic surfactant to be removed or in a slight excess amount.
- the proportion of organic solvent to water depends on the organic solvent utilized.
- the water content of the system is less than 50%, as in treatments (a) and (0) described herein.
- the solvents to be used are preferably those capable of completely dissolving the crude reaction product described. However, they may be those which are capable of dispersing the crude reaction product to such an extent that the reaction between the metallic salt and the anionic surfactant contained in the product may proceed without any substantial trouble.
- Such suitable solvents include, for example, water, methanol, ethanol, isopropanol, n-propanol, n-butanol, isobutanol, n-hexane, cyclohexane, benzene, toluene, chloroform, acetone, methyl ethyl ketone, methyl isobutyl ketone, dimethyl formamide, dimethyl sulfoxide, petroleum ether, diethyl ether, methyl acetate, ethyl acetate, propyl acetate, butyl acetate and the mixtures thereof.
- the amount of the solvent to be used may preferably be less than 50 times by weight of the SE solid.
- the metallic soap is a salt of a divalent or higher metal and the anionic portion of the anionic surfactant.
- the system after the completion of the double decomposition reaction comprises a sucrose ester of a fatty acid, a metallic salt of the surfactant formed by the double decomposition, a lay-produced salt, the non-reacted metallic salt, non-reacted sucrose and others.
- the sucrose ester of fatty acid and the metallic salt of the anionic surfactant remain in the system substantially in the form of a solidliquid phase with the sucrose ester of fatty acid being substantially in the form of a liquid layer and the metallic salt in a solid layer. Accordingly the sucrose ester of fatty acid and the metallic salt formed by the double decomposition of the surfactant are readily separated from each other by filtering the liquid-solid layers.
- SE and the metallic salt of the surfactant may remain in the system in the form of a liquid-liquid phase. For the separation of the liquid-liquid layers, centrifugation, decantation or any other conventional method may be utilized.
- the layer containing SE which is stripped of the metallic salt of the surface active agent is further stripped of other substances by distillation of the solvent and drying to obtain a high yield of sucrose ester of fatty acid.
- the organic layer containing SE thus obtained may be industrially used for certain purposes without any further treatment.
- the double decomposition reaction may be carried out at temperatures between to 100 (1., preferably at temperatures below 70 C., and at pH values between 6 to 10.
- a reaction at higher temperatures than 70 causes the thermal cracking of the sucrose ester of fatty acid.
- the optimum pH depends on the metallic salt used and the double decomposition products. Generally speaking, the lower the pH, the more preferable, but it must be higher than the pH value at which decomposition of the double decomposition salts is caused.
- the before mentioned treatment (c) is an alternative method for effectively carrying out the purification of sucrose esters of fatty acids.
- a high yield of sucrose esters of fatty acids is economically obtained by substantially quantitatively precipitating sucrose esters of fatty acids together with an organic or inorganic material easily soluble in water.
- the treatment (c) is also advantageously applicable for the purification of the crude reaction products obtained by the transparent emulsion method and the dimethyl-formamide method" mentioned before.
- Suitable solvents for the treatment (c) are above all ketones and esters.
- Ketones suitable for this purpose include acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl isoamyl ketone, methyl amyl ketone, diethyl ketone, ethyl-n-butyl ketone, ethyl amyl ketone, ethyl isoamyl ketone and others.
- Esters suitable for the purpose include methyl formate, ethyl formate, methyl acetate, ethyl acetate, isopropyl acetate, n-propyl acetate, isobutyl acetate, n-butyl acetate, amyl acetate, isoamyl acetate, methyl propionate, ethyl propionate' and others.
- solvents are immiscible with water so that the mixture of any of such solvents and water will be separated into two layers.
- the other solvents are miscible with water so as to form aqueous solvent solutions at any mixing ratio.
- Either type of solvents may be used for the invention. The selection of type depends on the properties of the crude reaction mixtures to be treated.
- the hydrated organic solvent may be used in an amount by weight between 1 and 20 times as much as the sucrose ester of fatty acid in solid form.
- An optimum amount of the hydrated organic solvent to be used in the treatment (c) depend on the properties of the solvent and the aliphatic groups of the sucrose esters of fatty acids.
- the proportion of the organic solvent to water depends on the organic solvent to be employed. Usually the water content of the system which is used for the purpose of the invention is less than 50%.
- the temperature at which sucrose esters of fatty acids are dissolved in the system containing water and an organic solvent are between 20 and 100 C. depending on the solvent to be used and aliphatic groups of the sucrose esters of fatty acids.
- the crude reaction mixture or the like to be treated is completely dissolved in the organic solvent, but the crude reaction mixture or the like may be dispersed in the organic solvent.
- sucrose esters of fatty acids is caused by the addition of a suitable water soluble organic or inorganic material to the system including the crude reaction mixture or the like. Any sucrose ester of fatty acid is precipitated out from the system as a result of the formation of a highly concentrated SE aqueous solution which may be produced due to the fact that the added water soluble material absorbs water in the system to form an aqueous solution, into which the sucrose ester of fatty acid in the organic solvent phase is dissolved.
- the water soluble material may be added in the form of an aqueous solution. Accordingly, it is essential for the material added to the system for precipitation to be easily soluble in water.
- Suitable Water soluble materials which may be used for this purpose are inorganic metallic and ammonium salts and saccharides.
- Water soluble inorganic metallic and ammonium salts may preferably include, for example, potassium chloride, sodium chloride, calcium chloride, magnesium sulfate, magnesium chloride, sodium sulfate, sodium hydrogensulfate, sodium sulfite, sodium thiosulfate, zinc chloride, potassium nitrate, sodium phosphates, sodium polyphosphates, sodium acetate, potassium carbonate, sodium lactate, barium lactate, ammonium nitrate, ammonium sulfate and others.
- Suitable organic materials are saccharides such as sucrose, dextrose, levulose and others. The water soluble material may be added in an amount from 1 to by weight of the sucrose esters of fatty acids contained in the system as based on a solid form thereof.
- the simultaneous precipitation of the water soluble material and sucrose esters of fatty acids is preferably carried out under the temperature conditions between -20 and 60 C. when a total recovery of sucrose esters of fatty acids is intended.
- the simultaneous precipitation of the water soluble material and sucrose esters of fatty acids is preferably carried out at a temperature of between 50 to 100 C. It should, however, be understood that the above temperature conditions are given by way of examples without intending to limit the temperatures thereof.
- sucrose esters of fatty acids together with the water soluble solvent may be carried out at a temperature other than the above mentioned range and it depends on the solvent used and aliphatic groups of the sucrose ester of fatty acid.
- Sucrose esters of fatty acid having smaller numbers of substituted fatty acid groups are more capable of forming an aqueous solution.
- mono-, di-, and tri-esters are successively transferred into aqueous solutions in that order.
- the precipitate obtained according to the treatment (c) means 21 SE concentrated aqueous solution and the appearance and form of the precipitate depends on the monoester content thereof and thet temperature at which the precipitation is carried out.
- the treatment (c) it is possible to recover and purify the SE precipitate formed by the addition of water soluble substance in a substantially quantitative manner and also to selectively recover, if desired, the monoester isolated from the SE precipitates.
- oil soluble impurities as anionic surfactant and unreacted methylester can be removed to the utmost extent.
- odorous as well as substances subject to taste have been substantially removed.
- the precipitation product thus obtained is in turn dried to the final product but it may be utilized as it is for certain purposes without any further treatment.
- the precipitate after the treatment (c) includes the Water soluble substance which may be removed, desired, by an appropriate manner to obtain a purer sucrose ester product.
- the treatment (a) is particularly effective for removing from crude reaction mixtures containing sucrose esters such water soluble materials as unesterified sucrose, coloring matters, odorous substances, inorganic salts and residual solvent.
- the treatment (b) is particularly effective for removing from the SE containing reaction mixtures unesterified sucrose and anionic surfactant, while the treatment (c) is particularly effective for removing therefrom such oil-soluble materials as acidified anionic surfactant, color-ing matters, nonreacted methyl ester and residual solvent.
- sucrose esters of fatty acids can be economically obtained on an industrial scale by selecting the most suitable combinations of these treatments depending on the composition of the SE crude reaction mixtures, the reaction used to form such mixtures, applications in which recovered sucrose esters of fatty acids to be used and impurities to be removed from the crude reaction mixtures. It is important to combine the treatments in such sequence that may best be suited for a given purpose.
- the regulation of water content in the organic layer means maintaining the water content in the organic layer within the specified range hereinabove discussed in the detailed descriptions taken in conjunction With each of the treatments (a), (b) and (c). A certain amount of water is normally introduced into the layer for this purpose. However, if the SE containing organic layer or precip itate obtained in the preceding treatment of the combined processes is found to include water in sufiicient amounts, it is no longer necessary to add a further portion of water.
- the regulation of the water content in the organic layer obtained in the treatment (a) is carried out prior to the step of adding a metal salt or its aqueous solution according to the treatment (b).
- oil-soluble materials such as acidified anionic surfactant, non-reacted methyl ester and the like which are left unremoved in the treatment (a) are completely taken out from the system to provide the sucrose ester of fatty acid in purest possible form.
- the regulation of the water content in the organic layer obtained in the treatment (a) is carried out before the step of adding a suitable water-soluble substance to the organic layer according to the treatment (c).
- the organic solvent for use in the treatment (c) is perferably selected from ketones and esters, and accordingly the same solvent may suitably be employed in the treatment (a). If a different solvent has been used in the treatment (a), it is desired to remove that solvent completely from the system and a new different solvent may then be introduced. This combined process can take out such oil-soluble materials as acidified anionic surfactant, non-reacted methyl ester and others which could not be removed by the treatment (a) alone.
- the regulation of the water content of the organic layer obtained by the treatment (b) is carried out before the step of adding a water soluble material to the organic layer according to the treatment (0).
- the same details and remarks on the selection of an organic solvent for use in the treatment (c) hereinabove discussed with respect to the combination of (a)+(c) may directly be applied to the selection of an organic solvent for use in this combined process.
- traces of oilsoluble impurities left unremoved in the treatment (b) are totally removed by the treatment (c).
- the liquidliquid extraction of the treatment (a) is applied to the precipitate obtained in the treatment (c).
- a fresh organic solvent is added to the precipitate obtained by the treatment (c) to form a further organic system and the water content of the further system is regulated so as to be adapted for the treatment (a).
- the adjustment of the pH of the further organic system is no longer necessary because the anionic surfactant has already been removed in the treatment (c).
- This combined process can remove the water-soluble substance such as unesterified sucrose, any by-product salt and others which are left behind in the precipitation in treatment (0) to provide sucrose esters of fatty acids in purest possible form.
- a fresh organic solvent is added to the precipitate obtained by treatment (c) to form a further system and the water content of the further system is regulated so as to be adapted for the treatment (b) in which a metallic salt or its aqueous solution is added to this thus prepared further system.
- This combined process can remove various water soluble substances contained in the precipitate obtained by the treatment (c) such as the water soluble material added in the treatment (0), non-reacted sucrose and any byproduced salt, whereby a further purified sucrose ester product is obtained.
- the treatment (a) is further followed by the step of fractionating the organic layer containing the extracted sucrose ester and then subjecting the fractionated layer to a recrystallization treatment to recover a sucrose ester precipitate.
- the system including the crude reaction mixture or the like is separated into an upper layer of the organic solvent and a lower aqueous layer by the liquid-liquid extraction operation and as the result of this operation substantially all of the sucrose ester of fatty acid and acidified surfactant are extracted into the upper solvent layer
- unesterified sucrose and any byprocess according to this embodiment of the invention contemplates further to separate the sucrose ester of fatty acid from the acidified surfactant in the fractionated organic layer. It has been found that this process including recrystallization is particularly adapted for the purification of the crude reaction mixtures obtained by the transparent emulsion method and having a relatively large content of the anionic surfactant.
- the recrystallization is effected by cooling down the fractionated organic layer containing the extracted SE to a temperature within the range of to 30 C.
- a fresh organic solvent may be added to the precipitate obtained by this recrystallization for a further recrystallization. This operation may further be repeated.
- the organic solvent may preferably be used in recrystallization in an amount of about 2 to parts for each part of the solid extract which will be obtained thereby.
- the sucrose ester of fatty acid is separated from the acidified surfactant and precipitated out in the organic layer due to the fact that the solubility of the sucrose ester tends to be reduced a lower temperature conditions during the recrystallization operation. Subsequent to this recrystallization, only a small fraction, i.e.
- the recrystallization should preferably be carried out at a temperature within the range of 0 to 30 C. as set forth above.
- the recrystallization must be conducted at a still lower temperature in order to obtain a satisfactory separation of the desired sucrose ester of fatty acid.
- the solvent which may exist in the precipitated or recrystallized sucrose ester of fatty acid is removed therefrom by a suitable technique to recover the powdery sucrose ester of fatty acid in purest possible form. In some applications the recrystallized sucrose ester of fatty acid is used as it is without removing the solvent therefrom.
- Suitable organic solvents which may be used in the crystallation stage of the present process are methyl ethyl ketone, methyl isobutyl ketone, methyl acetate, ethyl acetate, n-hexane, methanol, acetone and the mixtures thereof.
- n-butanol should be avoided because it tends to keep the sucrose ester of fatty acid in a solution form even at a more reduced temperature. It is possible to use for the recrystallation a different organic solvent from that used for the liquid-liquid extraction, although it should preferably be avoided as it makes the process more complicated and is disadvantageous for the recovery of the solvents.
- Suitable solvents for use in both procedures are those in which the sucrose ester of fatty acid is readily dissolved at a liquid-liquid extraction temperature within the range of 40 to 80 C. and difiicultly dissolved at a recrystallization temperature within the range of 0 to 30 C.
- Such solvents may include methyl ethyl ketone, methyl isobutyl ketone, methyl acetate, ethyl acetate, nhcxane and the mixtures thereof. Methyl ethyl ketone is particularly suitable for this purpose.
- methyl isobutyl ketone, ethyl acetate and n-hexane are all satisfactory as the organic solvent to be used in the present process and particularly, methyl ethyl ketone is more superior both in liquid-liquid extraction rate and recrystallization rate.
- the recrystallization is also useful for removing oil soluble materials such as acidified surfactant from the crude reaction mixtures containing sucrose esters of fatty acids with the result being an increased yield of such esters in purest possible form.
- any of the following pretreatments may be performed.
- Considerable amounts of anionic surfactant and unesterified sucrose are initially removed from the SE containing crude reaction mixtures by introducing the mixture into an organic solvent of the same kind as that to be used for the liquid-liquid extraction in the main process and by extracting the sucrose ester of fatty acid from the system through a solid-liquid extraction technique.
- the obtained extract may be introduced into the main process with or without the removal of the solvent therefrom. If this pretreatment has been conducted on the crude reaction mixture, a single cycle of the recrystallization procedure in the main process is sufficient to recover the desired sucrose ester of fatty acid in a satisfactory pure form.
- Another pre-treatment involves a removal of unesterified sucrose from the SE containing crude reaction mixture by adding water and an organic solvent for use in the liquid-liquid extraction of the present main process to the SE crude reaction mixture and by extracting the sucrose ester of fatty acid from the system through liquid-liquid extraction.
- this pre-treatment a substantial amount of unesterified sucrose included in the crude reaction mixture is removed therefrom into the aqueous layer.
- the obtained extract may be introduced into the main process with or without the removal of the solvent therefrom.
- the present invention is generally applicable to the purification of the crude reaction mixtures of sucrose esters or the like compositions containing any anionic surfactants, Whether they may be added for the production of the crude reaction mixtures or by-produced during the reaction operation for the production of the crude reaction mixtures.
- anionic sur factants which are used as emulsifiers for esterification, there may be included sodium, potassium and ammonium salts of fatty acids having from 12 to 22 carbon atoms; sodium and potassium salts of aromatic carboxylic acids; and alkyl sulfonate, alkyl sulfate, alkyl phosphate and alkyl benzene sulfonate, each having an aliphatic alkyl group of from 12 to 22 carbon atoms.
- fatty acids having from 12 to 22 carbon atoms can be removed as effectively as the above mentioned anionic surfactants.
- Sucrose esters of fatty acids obtained according to the present invention are tasteless, odorless, and innoxious and have HB values with a wide range so that their versatile use as non-ionic surface active agents can be realized.
- sucrose esters of fatty acids having residual radicals of fatty acids with 16 to 20 carbon atoms are useful as non-ionic surface active agents for the food additives.
- EXAMPE 1 500 parts of methyl ethyl ketone and 350 parts of water were added to 100 parts of a crude reaction mixture comprised 42% sucrose ester of stearic acid, 25% unesterified sucrose, 30% sodium oleate and 3% other constituents. The mixture was stirred vigorously at a temperature of 55 C. The mixture was stirred vigorously at a temperature of 5 C.
- Concentrated hydrochloric acid (37%) was added to the mixture in an amount sufficient to adjust the pH of the mixture at about 4.5.
- the mixture was then allowed to separate into two layers.
- the upper organic layer was found to have 42 parts of sucrose ester of stearic acid and 28 parts of acid dissolved therein, while the lower aqueous layer was found to contain 25 parts of unesterified sucrose and 6.7 parts of sodium chloride produced as the result of a reaction between hydrochloric acid and sodium oleate.
- the remaining upper organic layer was washed with 100 parts of hot water in order to take out traces of sucrose and sodium chloride.
- the solvent was then extracted out of the organic layer after which the remainder was dried under a reduced pressure to obtain 70 parts of solid mass.
- the solid mass contained 60% sucrose ester of stearic acid and 40% oleic acid.
- the yield of sucrose ester of stearic acid was as high as about 99.8%.
- EXAMPLE 2 2000 parts of methyl ethyl ketone and 500 parts of Water were added to 100 parts of a crude reaction mixture prepared by using the transparent emulsion technique, which reaction mixture comprised 41% sucrose ester of stearic acid, 26% unesterified sucrose, 30% potassium stearate and 3% other constituents. The mixture was stirred at an elevated temperature of 40 C. parts of bleaching powder was introduced into the system to cause a reaction in the system at a pH value of 9.0. A precipitate was formed in the system as the result of this reaction.
- the system including the precipitate was dried under a reduced pressure to finally obtain 43.6 parts of a solid mass of sucrose ester of stearic acid.
- the yield and purity of the sucrose ester were 97.8% and 92.0%, respectively.
- the product contains 57.0% monoester.
- EXAMPLE 3 500 parts of petroleum ether and 100 parts of water were mixed at a temperature of 30 C. with 100 parts of a SE containing mixture which comprised 40% sucrose ester of lauric acid, 32% unesterified sucrose, 25% sodium dodecylbenzenesulfonate and 3% others.
- the obtained reaction system was adjusted so as to have a pH of 9.0 and an aqueous solution of zinc sulfate was added dropwise to this system with stirring until the precipitation was concluded.
- the solution was isolated by a centifugal separator into an upper layer of petroleum ether and a lower Water layer containing the precipitate. After the removal of the lower layer, the upper layer was dried under a reduced pressure to finally obtain 38.4 parts of a slightly fluid, yellowish brown mass of sucrose ester of lauric acid. The yield of the sucrose ester was 93%. Further, the recovered sucrose ester had a purity 97% and contained 52% of monoester.
- sucrose ester of oleic acid was freed of water and thereafter dried to obtain 77.8 parts of a brown mass.
- This mass contained 70.2% sucrose ester of oleic acid, 19.1% unesterified sucrose, 8.1% potassium chloride and 2.6% remainder.
- the yield of sucrose ester of oleic acid was as high as 99.2%.
- Another mother liquor was prepared for carrying out a similar procedure and then cooled down to a temperature of 5 C. to cause precipitation.
- the formed precipitate was filtered out from the mother liquor at a reduced pressure and dried to obtain 3 8.8 parts of white powdery mass.
- This mass contained sucrose ester having a purity of 97.6%.
- the yield of sucrose ester was 90.3%.
- EXAMPLE 5 500 parts of methyl isobutyl ketone and 350 parts of water were added to 100 parts of a crude reaction mixture prepared by the transparent emulsion method and comprised of 41% sucrose ester of fatty acid of hardened beef tallow, 26% unesterified sucrose, 30% potas sium of fatty acid of beef tallow and 3% others. The mixture was stirred at a temperature of 70 C. The lower water layer was removed from the mixed solution using a separating funnel to obtain the upper organic solvent layer.
- sucrose ester of fatty acid of beef tallow and 36.0% Glaubers salt.
- the yield of sucrose ester was 81.0%.
- the solid mass A contained the sucrose ester of stearic acid having a purity of 99.2% and this sucrose ester included 86.2% of monoester, while the solid mass B contained sucrose ester of stearic acid having a purity of 97.1% with 24.9% monoester content.
- sucrose ester of greater monoester content could be obtained by the addition of suitable water-soluble compounds and by suitably adjusting the temperature conditions.
- EXAMPLE 7 1000 parts of ethyl acetate and 300 parts of water were added to 100 parts of a crude reaction mixture prepared by the dimethyl-formamide method and stripped of dimethyl formamide.
- the crude reaction mixture comprised 46.5% sucrose ester of fatty acid of hardened beef tallow, 43.8% unesterified sucrose, 2.1% non-reacted methyl ester, 5.6% fatty acid potassium salt of hardened beef tallow fatty acid and 2% others. The mixture was stirred at a temperature of 70 C.
- the lower Water layer was run ed and the upper organic solvent layer was first stripped of the solvent content and then dried under a reduced pressures to obtain 45.9 parts of solid mass.
- This solid mass contained the sucrose ester of fatty acid of hardened beef tallow having a purity ester of fatty acid of hardened beef tallow having a purity of 98.5% and a monoester content of 54.
- the yield was 97.2%.
- EXAMPLE 8 200 parts of methyl ethyl ketone and 200 parts of water were added to the organic layer obtained in Example 1. 4 parts of anhydrous calcium chloride was further added to the mixture keeping it at a temperature of 55 C. The pH of the system was adjusted from 4.5 to 6.0 by the gradual addition of caustic soda. After 30 minutes stirring the precipitate was filtered out from the system and the remaining filtrate was allowed to separate into an upper organic solvent layer and a lower water layer. Subsequent to the removal of water, the organic layer was subjected to a drying treatment to obtain 42.8 parts of solid mass containing the sucrose ester of stearic acid. The recovered sucrose ester had a purity of 97.5% and the yield thereof was 97.5%.
- the recovered solid mass contained 77.6% sucrose ester of stearic acid and 19.4% Glaubers salt. The yield of the sucrose ester was 95.2%.
- EXAMPLE 10 10 parts of sodium chloride was added to the organic layer obtained in Example 1 keeping the layer at the same temperature as in Example 1. The mixture was vigorously stirred.
- the system was then kept at a temperature of 0 C. for 30 minutes to cause precipitation.
- the precipitate was filtered and then dried to obtain 52 parts of solid mass.
- sucrose ester This mass was found to contain 78.9% sucrose ester of stearic acid and 19.2% sodium chloride. The yield of the sucrose ester was 97.7%.
- EXAMPLE 11 200 parts of ethyl acetate and 200 parts of water was introduced into the precipitate obtained by the addition of sodium chloride in Example 10. The mixture was heated at a temperature of 65 C. 2.0 parts of a 5% aqueous solution of calcium chloride was added to the system with stirring while keeping the system at a pH value of 8.0 by the addition of caustic soda. Upon the completion of the reaction, the precipitate and water layer were removed from the system and the remaining organic solvent layer was of the solvent.
- the layer was further dried under a reduced pressure to obtain 39.8 parts of solid mass.
- This mass contained sucrose ester of stearic acid having a purity of 99.2%.
- the yield of the sucrose ester was 94.0%.
- EXAMPLE 12 500 parts of hexane and 300 parts of water were added to parts of pulverized crude reaction mixture prepared by the transparent emulsion method and comprising 55% sucrose ester of fatty acid of beef tallow, 15% unesterified sucrose, 27% potassium oleate and 3% others. The mixture was heated at a temperature of 40 C. with stirring. While maintaining the reaction system at a pH of 7.5, an 'acqueous solution of zinc sulfate was added dropwise to the system until precipitation was halted. Upon the completion of the desired reaction, the system was separated by means of a centrifugal separator into an upper hexane layer and a lower water layer containing the precipitate. After the removal of the water layer, 300 parts of water was further added to the remaining hexane layer at a temperature of 60 C.
- the system was adjusted to a pH of 4.0 by the addition of diluted hydrochloric acid and then allowed to separate into organic and water layers for 30 minutes. The water layer was run off and the organic layer was washed with 500 parts of hot water.
- This solid mass contained the sucrose ester of fatty acid of beef tallow having a purity of 98.7%. The yield thereof was 98.7%.
- EXAMPLE 13 500 parts of ethyl acetate and 50 parts of water were added to 53.5 parts of solid mass obtained in Example 12. The mixture was heated to a temperature of 60 C. with stirring. After adjusting the pH of the system at 3.0 with diluted hyrochloric acid, 10 parts of sodium chloride was further introduced into the system. A continued stirring of the system precipitated a pasty substance A. The pasty substance A was recovered from the system and 5 parts of sodium chloride was added to the supernatant. The new system was heated with stirring and then cooled down to a temperature of 10 C. to recover a precipitate B.
- both the pasty substance A and the precipitate B were subjected to a drying treatment to obtain 49.5 parts of solid mass A and 15.5 parts of solid mass B respectively.
- the solid mass A contained 79.0% sucrose ester of fatty acid of beef tallow and 20.2% sodium chloride, while solid mass B contained 67.5% sucrose ester of fatty acid of beef tallow and 32.2% sodium chloride.
- the sucrose ester in the recovered mass B included 68% monoester and 32% di-and tri-esters.
- EXAMPLE 14 100 parts of ethyl acetate and 500 parts of water were added to 100 parts of a crude reaction product prepared by the transparent emulsion method which comprised 53.0% sucrose ester of fatty acid of solid beef tallow, 26.0% unesterified sucrose, 17.0% sodium salt of hardened beef tallow fatty acid and 4% other reaction residues.
- the mixture was heated at a temperature of 55 C. with stirring while keeping the pH of the system at 0.5 with caustic soda.
- Aqueous solution of ferric chloride was introduced dropwise into the system until the formation of a precipitate was completely halted.
- the organic solvent layer was separated from the system in a centrifigal separator.
- the precipitate thus obtained was further subjected to a drying treatment under a reduced pressure to recover 69 parts of a solid mass.
- This mass contained 74.6% sucrose ester of hardened fatty acid of beef tallow, 23.2% phosphate and 2.2% others.
- the yield of the sucrose ester was 97.2%.
- EXAMPLE 200 parts of ethyl acetate and 200 parts of water was added to the precipitate obtained in Example 14 and the mixture was stirred at a temperature of 55 C.
- the system thus formed was adjusted to a pH of 4.5 by the gradual introduction of diluted hydrochloric acid.
- the system was, when kept still, immediately separated into an upper organic solvent layer and a lower water layer. After the water layer was run off the system, the remaining organic solvent layer was washed with 200 parts of hot water. After removing the water, the washed organic layer was cooled down to a temperature of 10 C. to cause precipitation.
- the recovered precipitate was then subjected to a drying treatment to obtain 50.8 parts of white powdery mass.
- the powder contained the sucrose ester of fatty acid having a purity of 99%.
- the yield of the sucrose ester was 95%.
- EXAMPLE 16 1000 parts of methyl isobutyl ketone and 1000 parts of water were added to the precipitate obtained by the addition of Glaubers salt in Example 5. The mixture was stirred at a temperature of 50 C. While continuing thestirring at substantially the same temperature, the system thus prepared was adjusted to a pH of 4.0 with the gradual introduction of diluted hydrochloric acid. The system, when kept still in a separation funnel, was separated into an upper organic layer and a lower water layer. After removing the water layer from the system, the remaining orgainic layer was subjected to a drying treatment to obtain 35.5 parts of solid mass.
- This mass contained the sucrose ester of fatty acid having a purity of 90.7%.
- the yield of the sucrose ester was 78.5%.
- EXAMPLE 17 2000 parts of methyl isobutyl ketone and 1200 parts of water were added to 33.5 parts of the solid mass obtained in Example '16. The mixture was stirred at a temperature of 50 C. While keeping the system thus prepared at a pH of 8.0, 1.0 part of calcium hydroxide 18 was gradually introduced thereinto to cause the desired reaction.
- the system Upon the completion of the reaction, the system was isolated in a separating funnel into an upper organic solvent layer and a lower water layer. The water layer was first taken out and then the solvent was removed from the remaining organic layer. Thereafter the organic layer was subjected to a drying treatment to obtain 32.6 parts of solid mass.
- the recovered mass contained the sucrose ester of fatty acid having a purity of 98.2%.
- the yield was 78.0%
- EXAMPLE 18 300 parts of cyclohexane and 200 parts of water were added to the precipitate obtained in Example 5 as the result of the addition of Glaubers salt. The mixture was stirred at a temperature of 55 C.
- the system separated into an upper organic solvent layer and a lower water layer, when kept still, upon the conclusion of the desired reaction.
- the remaining organic layer was stripped of the solvent and then subjected to a drying treatment under a reduced pressure to obtain 34.4 parts of a solid mass.
- EXAMPLE 19 Water was introduced into the organic layer separated by the addition of the an aqueous solution of ferric chloride in Example 18. The mixture was heated to a temperature of 50 C.
- the system thus prepared was adjusted to a pH of 4.0 by the addition of phosphoric acid and kept still so as to separate into an organic solvent layer and a water layer. After the removal of the water layer, the remaining organic layer was stripped of the solvent and then subjected to a drying treatment to obtain 32.6 parts of solid mass.
- This solid mass contained the sucrose ester of fatty acid having a purity of 98%.
- the yield was 78%.
- EXAMPLE 20 The organic layer obtained in Example 1 was cooled down to a temperature of 10 C. to cause precipitation. The precipitate thus formed was recovered by filtration technique and thereafter subjected to a drying treatment to obtain 44 parts of solid mass.
- sucrose ester of stearic acid having a purity of 85.7%.
- the yield was 89.8%.
- the recovered sucrose ester comprised 55.0% monoester and 45.0% diand tri-esters.
- EXAMPLE 21 500 parts of n-hexane and 500 parts of water were added to 100 parts of the same crude reaction product as in Example 1. The mixture was heated to a temperature of 50 C. The system thus prepared was first adjusted to a pH of 4.0 with the introduction of 98% phosphoric acid and then kept still to be separated into an organic solvent layer and a water layer. After the removal of the water layer, the organic layer containing hexane was subjected to a recrystallization at a temperature of 10 C. 100 parts of methyl ethyl ketone was added to the precipitate recovered by the recrystallization. The new system was again subjected to a recrystallization treatment to cause precipitation. The recovered precipitate was dried under a reduced pressure to obtain 37.0 parts of white powder.
- This powder contained the sucrose ester of stearic acid having a purity of 95.0% and a monoester content of 55.0%. The yield was 86.0%.
- a water soluble substance selected from the group consisting of potassium chloride, sodium chloride, calcium chloride, magnesium sulfate, magnesium chloride, sodium sulfate, sodium hydrogensulfate, sodium sulfite, sodium thiosulfate, zinc chloride, potassium nitrate, sodium phosphates, sodium polyphosphates, sodium acetate, potassium carbonate, sodium lactate, barium lactate, ammonium nitrate and ammonium sulfate to recover the sucrose ester by precipitation, the organic solvent for this treatment being selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl isoamyl ketone, methyl amyl kctone, diethyl ketone, ethyl n-butyl ketone, ethyl amyl ketone, ethyl isoamyl ketone, methyl formate,
- the crude composition comprises about 10-80% sucrose ester, about 2-50% non-reacted sucrose, about 10-40% anionic surface active agent and 1% or less coloring and odor substances.
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JP859869A JPS4810448B1 (it) | 1969-02-05 | 1969-02-05 | |
JP7565269A JPS5037168B1 (it) | 1969-09-22 | 1969-09-22 | |
JP8707869A JPS5114487B1 (it) | 1969-10-29 | 1969-10-29 |
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US00009040A Expired - Lifetime US3748324A (en) | 1969-02-05 | 1970-02-05 | Method for the purification of sucrose esters of fatty acids |
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US (1) | US3748324A (it) |
BE (1) | BE745512A (it) |
DE (1) | DE2004899C2 (it) |
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Cited By (15)
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US4032702A (en) * | 1974-10-17 | 1977-06-28 | Tate & Lyle Limited | Production of surface active material |
US4104464A (en) * | 1975-04-18 | 1978-08-01 | Tate & Lyle Limited | Purification of sucrose esters |
US4683299A (en) * | 1984-08-10 | 1987-07-28 | Nebraska Department Of Economic Development | Sugar esters and an improved anhydrous method of manufacture |
US4710567A (en) * | 1984-08-10 | 1987-12-01 | Nebraska Department Of Economic Development, State Of Nebraska | Separation and purification of sugar esters synthesized from both aqueous and nonaqueous systems |
US4927920A (en) * | 1988-11-15 | 1990-05-22 | Nebraska Department Of Economic Development, State Of Nebraska, U.S.A. | Sugar ester synthesis |
WO1990011285A1 (en) * | 1989-03-17 | 1990-10-04 | Nebraska Department Of Economic Development, State Of Nebraska | Separation and purification of sugar esters |
US5008387A (en) * | 1988-04-18 | 1991-04-16 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Process for purifying sucrose fatty acid esters |
US5017697A (en) * | 1988-06-29 | 1991-05-21 | Dai Ichi Kogyo Seiyaku Co., Ltd. | Process for purifying sucrose fatty acid esters having high HLB |
EP0448996A1 (en) * | 1990-03-08 | 1991-10-02 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Process for removing soaps and fatty acids from sucrose fatty acid esters |
US20040063928A1 (en) * | 2001-01-18 | 2004-04-01 | Jo In-Ho | Preparation of aliphatic acid ester of carbohydrate |
US20100285913A1 (en) * | 2009-05-06 | 2010-11-11 | Burjes Roger W | Transmission With Dual IVT's And Planetary Gear Set |
US20130032748A1 (en) * | 2011-08-02 | 2013-02-07 | Hoke Ii Steven Hamilton | Liquid-Liquid Extraction Composition Useful In Processing Water-Soluble Surfactants |
CN103087118A (zh) * | 2013-02-28 | 2013-05-08 | 柳州高通食品化工有限公司 | 一种蔗糖脂肪酸酯的提纯方法 |
CN104004033A (zh) * | 2013-06-21 | 2014-08-27 | 浙江迪耳化工有限公司 | 一种蔗糖脂肪酸酯的提纯分离方法 |
CN115247009A (zh) * | 2022-06-28 | 2022-10-28 | 深圳市鸿合创新信息技术有限责任公司 | 玻璃表面易于书写的粉笔、其制备方法及用途 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5244803A (en) * | 1976-08-24 | 1977-04-08 | Dai Ichi Kogyo Seiyaku Co Ltd | Detergent compositions |
EP0065390A1 (en) * | 1981-05-11 | 1982-11-24 | TATE & LYLE PUBLIC LIMITED COMPANY | Purification of sucrose esters |
GB2163425A (en) * | 1984-08-10 | 1986-02-26 | Nebraska State | Separation and purification of sugar esters |
EP0434119B1 (en) * | 1989-12-21 | 1995-04-05 | Unilever N.V. | Process for refining soap-containing crude polyol fatty-acid polyester reaction products |
DE69428502T2 (de) * | 1993-12-24 | 2002-05-23 | Mitsubishi Chemical Corp., Tokio/Tokyo | Verfahren zur Herstellung von Saccharosefettsäureestern |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB826801A (en) * | 1957-08-29 | 1960-01-20 | Distillers Co Yeast Ltd | Recovery of sucrose esters |
DE1277833B (de) * | 1960-06-18 | 1968-09-19 | Spiess C F & Sohn | Verfahren zur Reinigung von Zuckerestern |
FR1291365A (fr) * | 1961-06-07 | 1962-04-20 | Spiess C F & Sohn | Procédé de purification des esters de sucre |
US3249600A (en) * | 1961-09-12 | 1966-05-03 | Ledoga Spa | Process for the preparation of purified sucrose esters and products obtained thereby |
NL145278B (nl) * | 1966-04-06 | 1975-03-17 | Nebraska State | Werkwijze ter uitvoering van een heresteringsreactie tussen een vloeibare polyhydrische alcohol en een hydrofobe ester van een vetzuur met lange keten. |
-
1970
- 1970-02-04 DE DE2004899A patent/DE2004899C2/de not_active Expired
- 1970-02-05 GB GB1295721D patent/GB1295721A/en not_active Expired
- 1970-02-05 FR FR7004164A patent/FR2032778A5/fr not_active Expired
- 1970-02-05 IT IT20234/70A patent/IT1001461B/it active
- 1970-02-05 US US00009040A patent/US3748324A/en not_active Expired - Lifetime
- 1970-02-05 BE BE745512D patent/BE745512A/xx not_active IP Right Cessation
- 1970-02-05 NL NL7001639A patent/NL7001639A/xx unknown
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4032702A (en) * | 1974-10-17 | 1977-06-28 | Tate & Lyle Limited | Production of surface active material |
US4104464A (en) * | 1975-04-18 | 1978-08-01 | Tate & Lyle Limited | Purification of sucrose esters |
US4683299A (en) * | 1984-08-10 | 1987-07-28 | Nebraska Department Of Economic Development | Sugar esters and an improved anhydrous method of manufacture |
US4710567A (en) * | 1984-08-10 | 1987-12-01 | Nebraska Department Of Economic Development, State Of Nebraska | Separation and purification of sugar esters synthesized from both aqueous and nonaqueous systems |
US5008387A (en) * | 1988-04-18 | 1991-04-16 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Process for purifying sucrose fatty acid esters |
US5017697A (en) * | 1988-06-29 | 1991-05-21 | Dai Ichi Kogyo Seiyaku Co., Ltd. | Process for purifying sucrose fatty acid esters having high HLB |
US4927920A (en) * | 1988-11-15 | 1990-05-22 | Nebraska Department Of Economic Development, State Of Nebraska, U.S.A. | Sugar ester synthesis |
WO1990011285A1 (en) * | 1989-03-17 | 1990-10-04 | Nebraska Department Of Economic Development, State Of Nebraska | Separation and purification of sugar esters |
EP0448996A1 (en) * | 1990-03-08 | 1991-10-02 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Process for removing soaps and fatty acids from sucrose fatty acid esters |
US20040063928A1 (en) * | 2001-01-18 | 2004-04-01 | Jo In-Ho | Preparation of aliphatic acid ester of carbohydrate |
US20100285913A1 (en) * | 2009-05-06 | 2010-11-11 | Burjes Roger W | Transmission With Dual IVT's And Planetary Gear Set |
US20130032748A1 (en) * | 2011-08-02 | 2013-02-07 | Hoke Ii Steven Hamilton | Liquid-Liquid Extraction Composition Useful In Processing Water-Soluble Surfactants |
US10413844B2 (en) * | 2011-08-02 | 2019-09-17 | The Procter & Gamble Company | Liquid-liquid extraction composition useful in processing water-soluble surfactants |
CN103087118A (zh) * | 2013-02-28 | 2013-05-08 | 柳州高通食品化工有限公司 | 一种蔗糖脂肪酸酯的提纯方法 |
CN103087118B (zh) * | 2013-02-28 | 2016-03-16 | 广西高通食品科技有限公司 | 一种蔗糖脂肪酸酯的提纯方法 |
CN104004033A (zh) * | 2013-06-21 | 2014-08-27 | 浙江迪耳化工有限公司 | 一种蔗糖脂肪酸酯的提纯分离方法 |
CN104004033B (zh) * | 2013-06-21 | 2016-08-10 | 浙江迪耳化工有限公司 | 一种蔗糖脂肪酸酯的提纯分离方法 |
CN115247009A (zh) * | 2022-06-28 | 2022-10-28 | 深圳市鸿合创新信息技术有限责任公司 | 玻璃表面易于书写的粉笔、其制备方法及用途 |
CN115247009B (zh) * | 2022-06-28 | 2023-08-22 | 深圳市鸿合创新信息技术有限责任公司 | 玻璃表面易于书写的粉笔、其制备方法及用途 |
Also Published As
Publication number | Publication date |
---|---|
FR2032778A5 (it) | 1970-11-27 |
GB1295721A (it) | 1972-11-08 |
DE2004899C2 (de) | 1984-07-26 |
NL7001639A (it) | 1970-08-07 |
BE745512A (fr) | 1970-07-16 |
DE2004899A1 (it) | 1970-09-03 |
IT1001461B (it) | 1976-04-20 |
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